Most dental resins are ester-based (meth)acrylate resin, which can be susceptible to hydrolytic degradation, especially when used in the presence of water and highly acidic conditions, such as self-etching adhesives. This in turn can impact the long-term performance or bounding durability. Therefore there is strong demand for hydrolytically-stable polymerizable resins or additives such as hydrolytically-stable polymerizable antibacterial resins or hydrolytically-stable and water-soluble cross-linkers.
The polymerizable acrylamide resins are known for its hydrolytic stability and N-substituted acrylamide resins were also known for its improved water solubility. CA 2250333, U.S. Pat. No. 6,172,131, and U.S. Pat. No. 6,350,839 disclose hydrolysis-stable and polymerizable acrylphosphonic acids for use as dental adhesive monomers. DE 273846 discloses polymerizable phosphonic amides. U.S. 2010/0076157 discloses a method for producing a polymerizable amide containing both carboxylic and phosphoric groups.